DE3689329T2 - Verbindungen auf der Basis der Phenylpyrimidine und sie enthaltende flüssigkristalline Zusammensetzungen. - Google Patents

Verbindungen auf der Basis der Phenylpyrimidine und sie enthaltende flüssigkristalline Zusammensetzungen.

Info

Publication number: DE3689329T2
Authority: DE; Germany
Prior art keywords: group; liquid crystal; acid; compound; smectic
Prior art date: 1985-12-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

DE19863689329

Other languages

German (de)

English (en)

Other versions

DE3689329D1 (de

Inventor

Ryoichi C O Central Re Higuchi

Hideaki C O Central Kawashima

Toru C O Central Res Kobayashi

Eri C O Central Res La Komatsu

Takao C O Central Res Sakurai

Tatsuru C O Central Tabohashi

Koji C O Central Res Takeuchi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Clariant Az (deutschland) Ag 65929 Frankfurt De

Original Assignee

Ajinomoto Co Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-12-04

Filing date

1986-12-02

Publication date

1994-07-07

1986-12-02 Application filed by Ajinomoto Co Inc filed Critical Ajinomoto Co Inc

1994-01-05 Publication of DE3689329D1 publication Critical patent/DE3689329D1/de

1994-07-07 Application granted granted Critical

1994-07-07 Publication of DE3689329T2 publication Critical patent/DE3689329T2/de

2006-12-03 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims description 50
239000000203 mixture Substances 0.000 title claims description 17
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239000004973 liquid crystal related substance Substances 0.000 claims description 25
239000004990 Smectic liquid crystal Substances 0.000 claims description 24
229910052799 carbon Inorganic materials 0.000 claims description 15
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 8
-1 Phenylpyrimidine compound Chemical class 0.000 claims description 7
125000004423 acyloxy group Chemical group 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 6
239000002253 acid Substances 0.000 description 27
230000010287 polarization Effects 0.000 description 9
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NPDBDJFLKKQMCM-UHFFFAOYSA-N tert-butylglycine Chemical compound CC(C)(C)C(N)C(O)=O NPDBDJFLKKQMCM-UHFFFAOYSA-N 0.000 description 1
239000010409 thin film Substances 0.000 description 1
UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
239000004474 valine Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3458—Uncondensed pyrimidines
- C09K19/3463—Pyrimidine with a carbon chain containing at least one asymmetric carbon atom, i.e. optically active pyrimidines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Liquid Crystal Substances (AREA)
Liquid Crystal (AREA)

DE19863689329 1985-12-04 1986-12-02 Verbindungen auf der Basis der Phenylpyrimidine und sie enthaltende flüssigkristalline Zusammensetzungen. Expired - Fee Related DE3689329T2 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP27283485		1985-12-04

Publications (2)

Publication Number	Publication Date
DE3689329D1 DE3689329D1 (de)	1994-01-05
DE3689329T2 true DE3689329T2 (de)	1994-07-07

Family

ID=17519419

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19863689329 Expired - Fee Related DE3689329T2 (de)	1985-12-04	1986-12-02	Verbindungen auf der Basis der Phenylpyrimidine und sie enthaltende flüssigkristalline Zusammensetzungen.

Country Status (3)

Country	Link
EP (1)	EP0225195B1 (fr)
JP (1)	JP2508037B2 (fr)
DE (1)	DE3689329T2 (fr)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5252252A (en) *	1983-09-10	1993-10-12	Merck Patent Gesellschaft Mit Beschraenkter Haftung	Anisotropic compounds and liquid crystal mixtures
DE3332692A1 (de) *	1983-09-10	1985-03-28	Merck Patent Gmbh, 6100 Darmstadt	Anisotrope verbindungen und fluessigkristallmischungen
DE3515374C2 (de) *	1985-04-27	1998-02-26	Hoechst Ag	Chirale getilte smektische flüssigkristalline Phasen und deren Verwendung in elektrooptischen Anzeigeelementen
DE3515373A1 (de) *	1985-04-27	1986-11-06	Merck Patent Gmbh, 6100 Darmstadt	Stickstoffhaltige heterocyclen
DE3518734A1 (de) *	1985-05-24	1986-11-27	Merck Patent Gmbh, 6100 Darmstadt	Smektische fluessigkristalline phasen
EP0257048B1 (fr) *	1986-02-17	1994-08-24	MERCK PATENT GmbH	Composes optiquement actifs
CA1341038C (fr) *	1986-03-10	2000-06-27	Masanao Kamei	Derive du fluoroalcane
DE3614778A1 (de) *	1986-05-02	1987-11-05	Merck Patent Gmbh	Smektische fluessigkristalline phasen
DE3618213A1 (de) *	1986-05-30	1987-12-10	Hoechst Ag	Chirale ester aus (alpha)-substituierten carbonsaeuren und mesogenen hydroxylverbindungen und ihre verwendung als dotierstoff in fluessigkristall-phasen
ES2019077B3 (es) *	1986-05-30	1991-06-01	Hoechst Ag	Esteres enantiomorfos de acidos carboxilicos alfa-sustituidos y compuestos hidroxilicos mesogenos y su empleo como material de dotacion en fases de cristal liquido.
DE3620049A1 (de) *	1986-06-14	1987-12-17	Hoechst Ag	Chirale ester aus (alpha)-substituierten phenylalkansaeuren und mesogenen hydroxylverbindungen und ihre verwendung als dotierstoff in fluessigkristall-phasen
US4980082A (en) *	1986-09-02	1990-12-25	Seiko Instruments Inc.	Ferroelectric SmC liquid crystal composition which comprises pyrimidinylphenyl ester compounds
JP2508125B2 (ja) *	1986-09-09	1996-06-19	味の素株式会社	フェニルピリミジン化合物及びこれを含有してなる液晶組成物
US5328639A (en) *	1986-11-10	1994-07-12	Canon Kabushiki Kaisha	Fluoroalkane derivative, its composition and liquid crystal device using the same
EP0268198B1 (fr) *	1986-11-20	1993-09-01	F. Hoffmann-La Roche Ag	Cristaux liquides ferroélectriques
JPS63165344A (ja) *	1986-12-26	1988-07-08	Chisso Corp	光学活性−２−メチルブチレ−ト類およびその利用物
DD257638A1 (de) *	1987-02-19	1988-06-22	Univ Halle Wittenberg	Ferroelektrische fluessigkristalle
DE3709549A1 (de) *	1987-03-24	1988-10-06	Hoechst Ag	Verwendung von 5-phenyl-pyrimidinderivaten als komponenten in smektischen fluessigkristallmischungen
DE3709618A1 (de) *	1987-03-24	1988-10-06	Hoechst Ag	Neue fluessigkristalline 5-phenylpyrimidin-derivate mit s(pfeil abwaerts)c(pfeil abwaerts)-oder s(pfeil abwaerts)c(pfeil abwaerts) -phase und verfahren zu ihrer herstellung
EP0285395B1 (fr) *	1987-03-31	1994-05-11	Ajinomoto Co., Inc.	Composés de phényl-pyrimidines cristaux liquides et compositions de cristaux liquides les contenant
DE3852422T2 (de) *	1987-04-27	1995-05-04	Chisso Corp	Optisch aktive 2-Biphenylpyrimidinderivate und diese enthaltende Flüssigkristallmischungen.
US4804759A (en) *	1987-05-27	1989-02-14	Adeka Argus Chemical Co., Ltd.	Pyrimidine compound
EP0307880B1 (fr) *	1987-09-19	1994-01-12	Hoechst Aktiengesellschaft	Mélanges liquides cristallins ferro-électriques
JPH01106870A (ja) *	1987-10-20	1989-04-24	Chisso Corp	２，５−ジフェニルピリミジン誘導体、液晶組成物および電気光学素子
JPH01106874A (ja) *	1987-10-21	1989-04-24	Chisso Corp	光学活性フェニルピリミジン化合物および液晶組成物
JPH0264194A (ja) *	1988-02-09	1990-03-05	Chisso Corp	強誘電性液晶組成物
JP2627918B2 (ja) *	1988-03-28	1997-07-09	チッソ株式会社	フルオロアルコキシジフェニルピリミジン、液晶組成物および電気光学素子
DE68926635T2 (de) *	1988-04-25	1997-01-02	Dainippon Ink & Chemicals	2,5-Disubstituierte Pyrazin-Derivate, Pyrimidin-Derivate und sie enthaltende Flüssigkristalle
US5244597A (en) *	1988-05-26	1993-09-14	Hoffmann-La Roche Inc.	Liquid crystalline mixtures having a chiral tilted smectic phase
DE4236104A1 (de) *	1992-10-26	1994-04-28	Hoechst Ag	Bifunktionelle Vorprodukte zur Herstellung von Flüssigkristallen
DE4324630A1 (de) *	1993-07-22	1995-01-26	Hoechst Ag	Smektische Flüssigkristallmischung
DE4423098A1 (de) *	1994-07-01	1996-01-04	Hoechst Ag	Verwendung von Pyrimidingruppen enthaltenden konjugierten Verbindungen als Elektrolumineszenzmaterialien
US6121448A (en) *	1995-03-28	2000-09-19	The Secretary Of State For Defence In Her Brittanic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland	Pyrimidine compounds
GB2316077B (en) *	1995-03-28	1999-09-08	Secr Defence	Pyrimidine Compounds
GB9506309D0 (en) *	1995-03-28	1995-05-17	Secr Defence	Pyrimidine compounds
JP3732255B2 (ja) *	1995-05-29	2006-01-05	株式会社半導体エネルギー研究所	反強誘電性液晶化合物および該化合物を含有する反強誘電性液晶組成物

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4609485A (en) *	1984-02-17	1986-09-02	Chisso Corporation	Bipyrimidinyl derivatives
JPS60218358A (ja) *	1984-04-13	1985-11-01	Ajinomoto Co Inc	液晶
JPS61129169A (ja) *	1984-11-27	1986-06-17	Teikoku Chem Ind Corp Ltd	液晶化合物
WO1986000087A1 (fr) *	1984-06-07	1986-01-03	Seiko Instruments & Electronics Ltd.	Compose de cristaux liquides
JPS61152659A (ja) *	1984-12-27	1986-07-11	Chisso Corp	１，４−ジピリミジニルベンゼン誘導体
JPS61197563A (ja) *	1985-02-27	1986-09-01	Chisso Corp	トリフルオロメチルフエニル基をもつピリミジン誘導体
DE3515373A1 (de) *	1985-04-27	1986-11-06	Merck Patent Gmbh, 6100 Darmstadt	Stickstoffhaltige heterocyclen

1986
- 1986-12-02 EP EP86309393A patent/EP0225195B1/fr not_active Expired - Lifetime
- 1986-12-02 DE DE19863689329 patent/DE3689329T2/de not_active Expired - Fee Related
- 1986-12-04 JP JP61289650A patent/JP2508037B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JPS62228068A (ja)	1987-10-06
DE3689329D1 (de)	1994-01-05
EP0225195A1 (fr)	1987-06-10
EP0225195B1 (fr)	1993-11-24
JP2508037B2 (ja)	1996-06-19

Legal Events

Date	Code	Title	Description
1994-12-22	8364	No opposition during term of opposition
2004-08-26	8327	Change in the person/name/address of the patent owner	Owner name: CLARIANT AZ (DEUTSCHLAND) AG, 65929 FRANKFURT, DE
2005-10-13	8339	Ceased/non-payment of the annual fee

Publication	Publication Date	Title
DE3689329T2 (de)	1994-07-07	Verbindungen auf der Basis der Phenylpyrimidine und sie enthaltende flüssigkristalline Zusammensetzungen.
DE3879380T2 (de)	1993-06-24	Ferroelektrische fluessigkristall-zusammensetzungen.
DE3627443C2 (fr)	1992-06-25
DD299989A5 (de)	1992-05-14	Flüssigkristallanzeigezelle
DE3785985T2 (de)	1994-01-20	Phenyl-Pyrimidin-Verbindung und flüssigkristalline Zusammensetzung.
EP0307880B1 (fr)	1994-01-12	Mélanges liquides cristallins ferro-électriques
DE3637084A1 (de)	1987-05-07	Propylenglykoldiether-derivate, fluessigkristallmischung und fluessigkristallvorrichtung
DE69107646T2 (de)	1995-08-24	Flüssigkristalline Verbindung und Flüssigkristallanzeigevorrichtung.
DE3783213T2 (de)	1993-04-29	Optisch aktive fluessigkristallverbindungen mit einer cyanogruppe.
DE3718174A1 (de)	1988-12-15	Verwendung von optisch aktiven oxiran-2-carbonsaeureestern als dotierstoffe in fluessigkristallmischungen, diese enthaltende fluessigkristallmischungen und neue optisch aktive oxiran-2-carbonsaeureester
DE68909631T2 (de)	1994-02-17	Ferroelektrische Flüssigkristallzusammensetzung.
DE3874633T2 (de)	1993-04-15	Ferroelektrische fluessigkristallzusammensetzung.
DE69109629T2 (de)	1995-10-19	Flussigkristallverbindung und Anzeigevorrichtung.
DE3885864T2 (de)	1994-04-28	Kondensate von optisch aktiven 4-(1-Hydroxy-äthyl)-biphenylen mit optisch aktiven organischen Säuren.
EP0520292A1 (fr)	1992-12-30	Dérivés d'azétidinones chirales et leur utilisation comme agents de dopage dans des mélanges de cristaux liquides
DE3889490T2 (de)	1994-12-01	Phenylpyrimidin-Flüssigkristall-Verbindungen und sie enthaltende Flüssigkristall-Zusammensetzungen.
DE69608895T2 (de)	2001-01-18	Polyzyklische verbindungen, daraus zusammengesetzte flüssigkristalline materialien, und sie enthaltende flüssigkristalline zusammensetzungen und eine flüssigkristallvorrichtung welche diese enthält.
DE69114730T2 (de)	1996-05-09	Flüssigkristallverbindung.
DE3886959T2 (de)	1994-05-11	1,2-Propandiolderivate.
DE3889408T2 (de)	1994-12-01	Flüssigkristalline Mischungen enthaltend optisch aktive 1-[2-Halogen-substituierte-phenyl]-äthanole und Derivate davon.
DE69309198T2 (de)	1997-10-16	Flüssigkristallverbindung
DD244351A5 (de)	1987-04-01	Verbindungen fuer ferroelektrische fluessigkristallvorrichtungen
DE68905883T2 (de)	1993-08-19	1-phenyl 1-propanol-derivate.
DE3873181T2 (de)	1993-01-14	Smektische fluessigkristallverbindung.
EP0532916B1 (fr)	1997-11-05	2-Fluoropyrazines, procédé pour leur préparation et leur utilisation dans des mélanges de cristaux liquides